GB962324A - Steroid compounds and production thereof - Google Patents
Steroid compounds and production thereofInfo
- Publication number
- GB962324A GB962324A GB3110160A GB3110160A GB962324A GB 962324 A GB962324 A GB 962324A GB 3110160 A GB3110160 A GB 3110160A GB 3110160 A GB3110160 A GB 3110160A GB 962324 A GB962324 A GB 962324A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- acid
- hydrogen atom
- amino group
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
The invention comprises 3-amino-steroids of the general formula: <FORM:0962324/C1/1> wherein R1 represents a group of one of the formulae -OH, -COCH3, -CHOHCH3, -COCH2OH, -COCH2OAc (Ac represents an acyl group derived from a carboxylic acid having less than 6 carbon atoms), -CHOHCH2 OH and: <FORM:0962324/C1/2> all having the b -configuration, R2 represents a hydrogen atom or a hydroxyl group having the a -configuration and represents a hydrogen atom when R1 represents a hydroxyl group, R3 represents two hydrogen atoms, a hydrogen atom and a hydroxyl group or an oxygen atom, X represents either hydrogen atoms in positions 4 and 5 or a double bond at position 4(5), the hydrogen atom at position 5 having the b -configuration, and Am represents a primary amino group, an aliphatic substituted amino group having less than 6 carbon atoms in the aliphatic substituent, or an araliphatic substituted, a cycloaliphatic substituted or a saturated heterocyclic ring substituted amino group, Am being a pyrrolidino group when X represents a double bond at the 4(5)-position, and acid addition and quaternary ammonium salts thereof; the preparation thereof and the corresponding compounds in which a hydrogen atom at the 5-position is in the alpha-configuration by treating the corresponding 3-keto compound with an amine of the formula AmH wherein Am has the above significance, and hydrogen in the presence of a hydrogenation catalyst, and by treating the corresponding 3-keto compound with the above amine of the formula AmH and formic acid, the amine being added first and allowed to react when the 3-keto reactant has a double bond at the 4(5) position and a free keto group in the side chain attached to the 17-position and, when required, converting the product into an acid addition salt with an acid or a quarternary salt by reaction with an alkyl ester of an acid. In the above hydrogenation process using benzylamine as the amine reactant, the hydrogenation may be continued to cause hydrogenolysis to form a steroid having a primary amino group at the 3-position. The above processes may be amplified in that a product containing a primary or secondary amino group may be acylated with an acid halide or acid anhydride of the formula R4COX or R4COO.COR4 respectively wherein R4 represents an aliphatic group having less than 6 carbon atoms and X represents a halogen atom to form the corresponding 3-acylaminosteroids. In addition, products prepared by the above processes having a primary amino group at the 3-position may be reacted with an aldehyde of the formula Ar.CHO wherein Ar represents a substituted or unsubstituted phenyl radical form a Schiff's base type of steroid compound having the general formula: <FORM:0962324/C1/3> wherein R1, R2, R3, X and Ar have the above significance. In all the above processes hydrolysis of ester groups present in the reactants may take place. In addition, the above process using formic acid as the reducing agent may result in the generation of formamide which causes the formation of cyclic orthoformic esters with reactants having a glycol grouping at the 20-and 21-positions. Products containing a 20-keto group may be reduced with lithium aluminium hydride or sodium borohydride to form a steroid having a 20-hydroxy group. Therapeutic compositions having an action on the central nervous system contain as the active ingredient a 3-amino-steroid prepared by the above process or a salt thereof, The compositions may be parenterally or orally. Specifications 740,568, 756,400, 763,835, 763,836, 779,001 and 779,002 are referred to.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR805106A FR1311761A (en) | 1959-09-12 | 1959-09-12 | Amino compounds of the steroid series and method of preparing such compounds |
FR830361A FR1455006A (en) | 1960-06-17 | 1960-06-17 | Amino-3 steroids and their preparation |
FR830360A FR89203E (en) | 1959-09-12 | 1960-06-17 | Amino compounds of the steroid series and method of preparing such compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
GB962324A true GB962324A (en) | 1964-07-01 |
Family
ID=27245322
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3110160A Expired GB962324A (en) | 1959-09-12 | 1960-09-09 | Steroid compounds and production thereof |
Country Status (2)
Country | Link |
---|---|
DE (1) | DE1189074B (en) |
GB (1) | GB962324A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2675821A1 (en) * | 2011-02-15 | 2013-12-25 | Ústav Organické Chemie A Biochemie Akademie Ved Ceské Republiky, v.v.i. | Pregnanolone derivatives substituted in 3alpha-position with the cationic group, method of their production, usage and pharmaceutical preparation involving them |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2494698A1 (en) * | 1980-11-21 | 1982-05-28 | Roussel Uclaf | NOVEL SUBSTITUTED 3-AMINO STEROID DERIVATIVES, THEIR SALTS, PREPARATION METHOD, MEDICAMENT APPLICATION AND COMPOSITIONS COMPRISING THE SAME |
-
1960
- 1960-09-09 GB GB3110160A patent/GB962324A/en not_active Expired
- 1960-09-09 DE DEE19901A patent/DE1189074B/en active Pending
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2675821A1 (en) * | 2011-02-15 | 2013-12-25 | Ústav Organické Chemie A Biochemie Akademie Ved Ceské Republiky, v.v.i. | Pregnanolone derivatives substituted in 3alpha-position with the cationic group, method of their production, usage and pharmaceutical preparation involving them |
EP2675821B1 (en) * | 2011-02-15 | 2018-04-18 | Ústav Organické Chemie A Biochemie Akademie Ved Ceské Republiky, v.v.i. | Pregnanolone derivatives substituted in 3alpha-position with the cationic group, usage and pharmaceutical preparation involving them |
Also Published As
Publication number | Publication date |
---|---|
DE1189074B (en) | 1965-03-18 |
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